Hydrochloric Acid → Asp-9521

HRID 1894947ノート

反応式

HRID 1894947 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([OH:14])=O)=[CH:6]2.[CH3:15][C:16]([OH:25])([CH3:24])[CH2:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([N:21]1[CH2:22][CH2:23][CH:18]([CH2:17][C:16]([CH3:24])([OH:25])[CH3:15])[CH2:19][CH2:20]1)=[O:14])=[CH:6]2

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 204015-Methoxyindole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184234282-Methyl-1-(piperidin-4-yl)propan-2-ol

生成物 1

HCID 25210792Asp-9521収率 82.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 478 mg of 5-methoxyindole-2-carboxylic acid and 432 mg of 2-methyl-1-(piperidin-4-yl)-2-propanol in 8 mL of DMF were added 575 mg of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride and 169 mg of 1-hydroxybenzotriazole, followed by stirring at room temperature for 1 day. 0.2M aqueous hydrochloric acid was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with 0.2M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol=1:0-24:1], and then crystallized from a mixture of ethyl acetate/diisopropyl ether to obtain 683 mg of 1-{1-[(5-methoxy-1H-indol-2-yl)carbonyl]piperidin-4-yl}-2-methylpropan-2-ol as a white crystal.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 0.2M aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform:methanol=1:0-24:1]
  6. customcrystallized from a mixture of ethyl acetate/diisopropyl ether

出典と根拠

ORDレコード
ord-e1384e6c2519432a86f90b80e9d21c45
出典データセット
uspto-grants-2013_08
特許番号
US08513422B2

反応ノート

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